Water → HCID 131729007, compound

Participants

Reaction Conditions

Reaction Steps

500 mg of the compound [1-1] was dissolved in 10 mL of tetrahydrofuran and cooled to −78° C. Thereafter, 2.33 mL of n-butyllithium (1.57M hexane solution) was added thereto. After the 1 hour stirring at the same temperature, 193 μL of picolinaldehyde was added to the resulting white suspension, and the suspension was stirred overnight while heating back to room temperature. 50 mL of water was added to the reaction mixture, and the mixture was extracted with 200 mL of ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70) to obtain 212 mg of tert-butyl((1S)-1-{4-[hydroxy (pyridin-2-yl)methyl]phenyl}ethyl)carbamate [12-1] (hereinafter, referred to as the compound [12-1]) as a light brown oily product.

Provenance & Evidence